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Located on the scenic Chester River, the historic town is home to great restaurants and a vibrant arts community. Our guest rooms and secluded cottages offer unparalleled privacy with wood-burning fireplaces and modern ensuite bathrooms.

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Check out our Calendar of Events! Brampton Inn has a total of 13 rooms: Seven spacious guest rooms and suites in our beautiful manor house and six separate axult.

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The spacious accommodations have been appointed with your comfort in mind. They provide privacy and outdoor green spaces to enjoy.

Brampton Inn also offers two dog-friendly rooms: Your perfect Eastern Shore vacation starts at the Brampton Inn! Did you know that the Eastern Shore of Maryland is also one of the best birding areas in the U.

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Our outdoor boutique wedding venue can host wedding parties of up to adult dates in Chester Maryland people or an elopement for just the two of you. Whether you want a small front-porch ceremony Cgester a casual brunch wedding, our wedding and elopement packages can help you plan your big day with ease!

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Our luxurious Chestertown, MD, Bed and Breakfast and cottages are perfect for a midweek or weekend escape. Want something special added to your vacation without the extra hassle of organizing the details? Look no further!

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The newest accommodation at our Chestertown Bed and Breakfast is a chic, contemporary adhlt bedroom flat.

Excellent restaurants, gorgeous views, and exciting festivals are …. Picture yourself on the deck of a spacious sailboat, the wind blowing your hair, as you enjoy picturesque views of the Chesapeake Bay.

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Seasonal Specials. Welcome to Our Maryland Inn!

Explore Our Accommodations. Get Our Free Guide. Say "I Do" to a Brampton Wedding.

View Our Inclusive Packages. Add-Ons Want something adult dates in Chester Maryland added to your vacation without the extra hassle of organizing the details? Add Something Special to Your Stay. Yellow Room Bright, grand and spacious, 2nd floor room that features huge walnut windows with views of the garden. Green Room This spacious third Chestre room at our romantic bed and breakfast in Maryland, has many windows, all with treetop views.

The Apartment in the Woods The newest accommodation at our Chestertown Bed and Breakfast is a chic, contemporary one bedroom flat. More Posts.